Variamycin
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| Category | Antibiotics |
| Catalog number | BBF-02744 |
| CAS | 12677-11-1 |
| Molecular Weight | 1085.14 |
| Molecular Formula | C52H76O24 |
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Description
Variamycin is a glycoside antibiotic originally isolated from Streptomyces olivovariabilis 6604-9. It has the effect of resisting gram-positive bacteria, fungi and tumors.
Specification
| Synonyms | Variamitsin; Varamycin; NSC 269146; Antibiotic 6604-9A; 3(C)-Demethyl-4(C)-O-methylmithramycin |
| IUPAC Name | 3-(3,4-dihydroxy-1-methoxy-2-oxopentyl)-6-[4-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-2-[5-hydroxy-4-[5-hydroxy-4-(4-hydroxy-5-methoxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-7-methyl-3,4-dihydro-2H-anthracen-1-one |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(OC(C2O)C)OC3=CC4=CC5=C(C(=O)C(C(C5)C(C(=O)C(C(C)O)O)OC)OC6CC(C(C(O6)C)O)OC7CC(C(C(O7)C)O)OC8CC(C(C(O8)C)OC)O)C(=C4C(=C3C)O)O)O)O |
| InChI | InChI=1S/C52H76O24/c1-18-30(72-36-15-31(44(59)21(4)68-36)73-34-13-28(54)43(58)20(3)67-34)12-26-10-25-11-27(51(66-9)49(64)42(57)19(2)53)52(48(63)40(25)47(62)39(26)41(18)56)76-38-17-33(46(61)23(6)70-38)75-37-16-32(45(60)22(5)69-37)74-35-14-29(55)50(65-8)24(7)71-35/h10,12,19-24,27-29,31-38,42-46,50-62H,11,13-17H2,1-9H3 |
| InChI Key | NKGFIFLSQXHQOK-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi; neoplastics (Tumor) |
| Boiling Point | 1155.7±65.0°C at 760 mmHg |
| Density | 1.47±0.1 g/cm3 |
Reference Reading
1. Cross resistance pattern towards anticancer drugs of a human carcinoma multidrug-resistant cell line
R S Gupta, W Murray, R Gupta Br J Cancer. 1988 Oct;58(4):441-7. doi: 10.1038/bjc.1988.237.
Puromycin-resistant (PurR) mutants/variants of a human carcinoma cell line (HeLa), which show greatly reduced cellular uptake of 3H-puromycin and 3H-daunomycin have been isolated after one- and two-step selections in presence of the drug. The cross-resistance pattern of these mutant cell lines towards numerous anticancer drugs and other inhibitors has been examined. Both the first- and the second-step mutants exhibited increased resistance to a number of antimitotic drugs (viz. vinblastine, vincristine, colchicine, taxol and maytansine), several protein synthesis inhibitors (viz. chalcomycin, bruceantin, harringtonine, homoharringtonine), a large number of DNA interactive compounds (viz. aclacinomycin A, actinomycin D, adriamycin, m-AMSA, chromomycin A3, coralyne sulphoacetate, daunomycin, ellipticine, mithramycin, mitoxantrone, 5-methoxysterigmatocystin, rubidazone, variamycin, VM26 and VP16-213) and a number of other drugs acting via other mechanisms (viz. Baker's antifol, nitidine chloride and rhodamine 123). Whereas the first-step mutants showed stable resistance to these drugs, the second-step lines partially reverted upon growth in non-selective medium. Further, treatment of these mutant lines with non-cytotoxic doses of the calcium channel blocker verapamil reverted or abolished their resistance to the above drugs in a dose-dependent manner. In contrast to the above compounds, the PurR mutants showed no significant cross-resistance to a large number of other drugs which included asaley, AT-125, 5-azacytidine, azaserine, cyclocytidine, cis-platin, cytosine arabinoside, chlorambucil, chlorpromazine, alpha-difluoromethyl ornithine, 5-fluorouracil, ftorafur, gallium nitrate, hydroxyurea, ICRF-159, ICRF-187, imipramine, methotraxate, 6-methylmercaptopurine riboside, mycophenolic acid, melphalan, mitomycin C, methyl GAG, nafoxidine, reumycin, 6-selenoguanosine, 6-thioguanine, tiazofurin, tamoxifen, thalicarpine, tiapamil and verapamil). These cross-resistance data should prove useful in developing suitable drug combinations to which cellular resistance would not develop readily.
2. [Effect of the antibiotic variamycin on the growth of a rabbit brain tumor]
L I Kondakov, A S Khalanskiĭ, T G Terent'eva, L Ia Iablonovskaia Antibiot Med Biotekhnol. 1986 Aug;31(8):620-4.
The effect of variamycin, an antibiotic of the group of aureolic acid on development of dedifferentiated astrocytoma of the brain was studied on rabbits. The antibiotic was administered intraperitoneally in a dose of 0.1 mg/kg daily for 6 days. The interval between the 6-day courses was 7 days. The results were estimated by changes in duration of the latent period of the tumor development in comparison to those in the controls. One course of the treatment with variamycin started late after the tumor transplantation, i. e. on the 18th day, resulted in an increase in the latent period duration by 25.7 per cent. Starting of the treatment with the antibiotic on the 6th day after the tumor transplantation resulted in an increase in the latent period duration by up to 69 or 74 per cent with the use of 2 or 3 treatment courses, respectively. The histological examination revealed pronounced dystrophic changes or complete resorption of the tumor tissue due to variamycin effect.
3. [Structure of the antineoplastic antibiotic variamycin]
A S Shashkov, D V Iashunskiĭ, Iu V Zhdanovich, G B Lokshin Bioorg Khim. 1991 Mar;17(3):410-6.
The results of the structural study of antitumor antibiotic variamycin and its peracetyl derivative by 1H-and 13C-NMR spectroscopy are reported. Structures of carbohydrate chains of the antibiotics molecule are revised. Variamycin is shown to be 2-[beta-cymmarosyl(1-3)-beta-oliosyl (1-3)-beta-olivosyl]-6-[beta-olivosyl (1-3)-beta-olivosyl] chromomycinone.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
